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Executive Assistant & Operations Coordinator
Guest & Operations Specialist
 

Executive Assistant & Operations Coordinator

Location: Cape Cod, MA (Hybrid – must be local)
Schedule: Full-Time (3-40 hours/week)
Compensation: $25–$35/hour, based on experience

About the Role
The Nauset Rental leadership team is searching for a sharp, trustworthy, and tech-savvy Executive Assistant & Operations Coordinator to support our Exec Team and help run the day-to-day with independence and efficiency.

This is a high-trust, high-autonomy role for someone who thrives on taking ownership, solving problems proactively, and keeping a fast-moving operation organized and on track. You’ll be responsible for removing friction — not just executing tasks, but closing loops and anticipating needs before they escalate.

AI-First Expectations
We are an AI-forward company. In this role, you’ll be expected to use AI and lightweight automation to reduce manual work over time (targeting ~30–50% reduction in repetitive lift). You don’t need to code, but you should be excited to:

• Use AI daily for drafting, research, and problem-solving
• Build or maintain simple automations (onboarding, follow-ups, reminders)
• Improve systems so work becomes easier and more scalable

What You’ll Do

Executive Support

• Manage inbox and calendar, including prioritization, scheduling, follow-ups, and tracking meeting action items
• Keep the Exec Team on track during onboarding, tech transitions, and launches
• Research tasks and present clear recommendations (e.g., benefit options, vendor tools, pricing, timelines)
• Provide lightweight personal admin support as needed, including household logistics, scheduling, vendor coordination, and managing small tasks end-to-end

Operations & Admin Coordination

• Own new hire admin onboarding (email, HubSpot, password manager, access, checklists)
• Manage basic system access issues before escalating
• Coordinate vendors, contracts, purchases, and payments; use judgment to clarify true requirements and keep work moving without unnecessary escalation
• Chase invoices, rent checks, approvals, and outstanding responses until resolved
• Liaise with the VA on deliverables and timelines
• Support confidential HR administration

Office & Local Support

• Manage office logistics and supplies, and support team moments such as birthdays, client and staff holiday gifts, and team gatherings
• Run occasional local errands or vendor visits
• Flex into limited field support during peak season as needed

What You Bring

• Experience as an executive assistant, office manager, or operations coordinator
• High discretion and integrity
• Strong judgment, follow-through, and comfort operating independently
• Tech-savvy and comfortable with admin systems (HubSpot, Google Workspace, Slack, AI tools all a plus)
• Local to Cape Cod and able to be in-person when needed

Growth Path
Opportunity to expand into broader operations, HR, or leadership support over time.

How to Apply
If you’re interested, please email [email protected] with your resume and a brief note about you, answering one of the prompts below:
Tell us about a time you anticipated a problem before it escalated. What signals did you notice, and what did you do?
Describe a workflow or task you improved using AI, automation, or better systems. What was the impact?
Share an example of when you pushed back (professionally) on a vendor or internal request to keep things moving.
 

Guest & Operations Specialist

Location: Brewster, MA (Hybrid option – Cape Cod & South Shore preferred)
Type: Full-Time, Year-Round
Schedule: Includes weekends and holidays during peak season; on-call rotation required during summer. Flexibility for a Tuesday–Saturday or weekend-inclusive year-round schedule. 

About the Role
We're hiring for multiple full-time Guest & Operations Specialists to support our fast-growing vacation rental business. This is a hands-on, core role focused on guest experience, reservations, and internal operations coordination. You’ll be part of a close-knit team where clear communication, follow-through, and ownership matter. We work hard, share a lot of laughs, and are genuinely excited about where we’re headed. If you're looking to build your career, want to contribute meaningfully, and are ready to jump in wherever needed—you’ll thrive here.

What You’ll Do

• Handle guest operations from reservation inquiry through post-stay follow-up—including bookings, communication, and in-stay support
• Be a go-to contact for both guests and homeowners—keeping things smooth, calm, and professional
• Manage and maintain accurate property listings and internal systems
• Assist with vendor coordination, seasonal staff scheduling, or office logistics as needed
• Join the summer on-call rotation and be prepared for shifting schedules during peak season
• Pitch in wherever the team needs support—this is a role where no two days look the same

What We’re Looking For

• Organized, detail-oriented, and able to follow through on tasks without micromanagement
• A problem-solver who can anticipate issues and stay calm under pressure, with the ability to navigate difficult conversations with tact and confidence.
• Comfortable managing high-demand customer service situations with professionalism and resilience—especially during peak season
• Comfortable with tech, communication tools, and open to using AI or automation tools to work smarter
• Interested in growth—but also excited to be part of the core team that runs the business day to day
• Willing to work weekends and holidays in season, and possibly a Tuesday–Saturday or weekend-inclusive year-round schedule. A “GSD” mentality is a must
• Cape or South Shore candidates who can be in the Brewster office at least 3 days a week, with some flexibility based on the time of year

Why Work With Us
We’re a small, committed team that values accountability, clear communication, and high standards. The work can move quickly—especially in-season—but we support each other and take pride in what we deliver. There’s exciting room to grow here, and we aim to promote from within when we see team members stepping up. 

Focus Areas & Growth Potential
Guest services is the foundation of this role, but we’re also looking for team members who can contribute in other key areas from day one. As we scale across the Cape and improve our systems and operations, there’s room to grow into areas like:

• Office operations & vendor coordination
• Sales & Marketing support
• Process optimization & systems thinking
• New tech implementation & automation
• Guest services management
• Staff onboarding & training

These aren’t the only directions—we’re building a well-rounded team with complementary strengths. Let us know where you’d be excited to contribute now, and where you see yourself growing next.

Compensation & Benefits

• Competitive salary based on experience
• 401(k) with company match
• Paid time off & paid holidays
• Hybrid work setup (in-office + remote)
• Additional benefits are under evaluation as we grow.

How to Apply
Email [email protected] with your resume and a brief note about why this role is the right fit. We get plenty of generic applications—take a minute to tell us something real. Bonus points if you include a reference to “GSD” or tell us about a time you owned a process or solved a tough problem. We're looking for contributors, not just task-takers.